He was seen chatting on his phone during the dinner, but soon turned his attention back to his friends.
All smiles, he seemed to be enjoying his evening, whilst Rosee kept him entertained.
Drake's outing comes as his girlfriend Jennifer is said to be "head over heels".
The couple went public with their romance in December, and it appears to be moving at a fast pace.
A source told Entertainment Tonight: "She's head over heels for Drake. It's a new relationship, but she really likes him. She's really into him."
And Jennifer revealed the pair have been in the studio recording new music together.
Asked about her new project with Drake at a Shades Of Blue TCA panel, she simply said: "He just asked me to do a song with him and that's what we've been doing. We'll see if it's on his next album."
While Jennifer is now ready to get serious about Drake, she initially wanted to keep their romance "easy, light and fun" as she worried he was a "player."
The insider continued: "The last thing Jennifer wants is for Drake to do something to make her look foolish or feel like she has been played."
Jennifer has eight-year-old twins Emme and Max with her former husband Marc Anthony and recently revealed she felt extremely lucky to have 'wonderful people' in her life.
She said: "Nobody does anything alone. Even with the kids, it takes a village."
MailOnline has contacted a representative for Drake for comment.